As part of an effort on high performance/high temperature polymers for functional and aerospace structural applications, the reaction of aromatic diacetylenic diketones with various monomers is under investigation.
There are several reports in the literature on the preparation of polyenamine ketones. Ueda and co workers prepared polyenamine ketones from the reaction of diamines with 1,6-diethoxy-1,5-hexadiene-3,4-dione [M. Ueda, K. Otaira and Y. Imai, J. Polym. Sci. Polym. Chem. Ed. 16, 2809 (1978)]and 2,2'-disubstituted bis(4-ethoxymethylene-5-oxazolone [M. Ueda, K. Kino, T. Hirono and Y. Imai, J. Polym. Sci. Polym. Chem. Ed. 14, 931 (1976)]. These low molecular weight polyenamine ketones exhibited initial onset of weight loss by thermogravimetric analysis (TGA) in a nitrogen atmosphere at 200.degree.-300.degree. C. Pavlisko and co workers reported the preparation of polyenamine ketones for the reaction of bis(1,3-diones) and diamines [J. A. Pavlisko, S. J. Huang, and B. C. Benicewicz, J. Polym. Sci. Polym. Chem. Ed. 20, 3079 (1982)]. These polymers were prepared in N-methylpyrrolidone using an acid catalyst with inherent viscosities in the range of 0.25-0.36 dL/g. Polyenamine ketones are not at present commercially available.
Poly(enamine-esters) comprise a second type of polymer containing the enaminocarbonyl system. The preparation and characterization of a number of such systems including some containing siloxane units has been reported by Moore and co-workers. [J. A. Moore and J. E. Kochanowski Macromolecules 8, 121 (2975); J. A. Moore and T. O. Mitchell J. Polym. Sci. Polym. Chem. Ed. 18, 3029 (1980) and 21, 1305 (1983)].
It is therefore an object of the present invention to provide novel polyenamine ketones having improved physical property characteristics.
Another object of the present invention is to provide high molecular weight polyenamine ketones that can be solution cast to form films having improved mechanical properties.
A further object of the present invention is a process for preparing high molecular weight polyenamine ketones.
Another subject of the present invention is a process for preparing solution of polyenamine ketones that can be directly used to prepare prepregs, adhesive tapes, film and coatings.